Toluene → HCID 22417836, compound

HRID 1720280Notes

Reaction equation

HRID 1720280 reaction equation
[ClH:1].[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:22]3[C:17](=[C:18]([O:23]C)[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].C1(C)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>O>[OH2:23].[ClH:1].[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:22]3[C:17](=[C:18]([OH:23])[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 22417935HCID 22417935, compound

Product 1

HCID 22417836HCID 22417836, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flame dried single-neck round bottom flask equipped with a Dean-Stark trap and a condenser, a solution of 1.0 g (2.9 mmol) of N-(4-butylphenyl)-8-methoxyquinolin-4-amine hydrochloride and 20 mL of toluene was treated with 1.9 g (14.5 mmol) of anhydrous aluminum chloride. This was heated under reflux for five hours, and then allowed to cool to room temperature. The reaction solution was treated dropwise with water until a sticky solid formed. Work-up of the mixture eventually afforded mg of crude product. This was recrystallized from water-formic acid to furnish 340 mg (34%) of the title compound: m.p. 269° C.

Workup

  1. customIn a flame dried single-neck round bottom flask
  2. customequipped with a Dean-Stark trap and a condenser
  3. temperatureThis was heated
  4. temperatureunder reflux for five hours
  5. customformed
  6. customThis was recrystallized from water-formic acid

Sources & evidence

ORD record
ord-c0ba644a6ebf4b9e9ac674cb3cdd6c62
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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